In the season premiere, Pee-wee talks about the importance caring for one's teeth. Jambi calls from his trip to Mount Rushmore. Pee-wee gets a toothache and tries everything to get it to stop hurting. Miss Yvonne talks Pee-wee into going to the dentist, but he is afraid to go, so Miss Yvonne goes with him; it turns out that Pee-wee had a baby tooth that needed to come out.
- Miss Yvonne visits in this episode.
- First time Jambi is seen outside his box.
- When Pee-wee passes Mount Rushmore at the end, Jambi is seen in front of Abraham Lincoln's head.
- Secret word: it
- Connect-the-dots: rocket
- Snack: carrot
- Wish: Pee-wee tries to wish that his tooth would stop hurting, but Jambi is not there and an answering machine is in his box instead.